Reactions of organic peroxides. Part XVII. Hydroperoxides from cyclohexanone cyclohexylhydrazone and hydrazocyclohexane

Abstract

Solutions of cyclohexanone cyclohexylhydrazone, on treatment with air or oxygen, provided crystalline 1-hydroperoxyazocyclohexane; by-products included a dehydro-dimer and compounds derived from hydroperoxide decomposition. Thermal decomposition of the hydroperoxide gave cyclohexanol, cyclohexanone, bicyclohexyl, and cyclohexanone azine, whereas reaction with sulphuric acid afforded cyclohexanone, hydrazine sulphate, and dicyclohexylidene diperoxide. Hydrazocyclohexane absorbed oxygen extremely rapidly, with formation of the 1-hydroperoxide, which was converted into hydrogen peroxide and azocyclohexane on addition of water.